


A Little Help from the Party

by Stranger_Scribe



Category: Stranger Things (TV 2016)
Genre: Anal Fingering, Anal Play, Anal Sex, Double Penetration, F/M, Fivesome - F/M/M/M/M, M/M, Multi, Oral Sex, Rimming, Strap-Ons
Language: English
Status: Completed
Published: 2020-11-01
Updated: 2020-11-01
Packaged: 2021-03-08 22:28:30
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 6,446
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27324259
Author URL: https://archiveofourown.org/users/Stranger_Scribe/pseuds/Stranger_Scribe
Summary: Max can't fit her new strap-on in Lucas's ass, so she enlists of the help of Will, Dustin and Mike to help train his hole. Total smut involving the five teens.
Relationships: Dustin Henderson/Maxine "Max" Mayfield/Lucas Sinclair, Maxine "Max" Mayfield/Lucas Sinclair, Maxine "Max" Mayfield/Lucas Sinclair/Mike Wheeler, Will Byers/Dustin Henderson/Maxine "Max" Mayfield/Lucas Sinclair/Mike Wheeler, Will Byers/Maxine "Max" Mayfield/Lucas Sinclair
Comments: 7
Kudos: 11





	A Little Help from the Party

**Author's Note:**

  * For [ajson123456](https://archiveofourown.org/users/ajson123456/gifts).



Lucas gasped in pain as Max tried to push the strap-on into his ass. No matter how much lube they added, the stiff sex toy was simply too much. Max sighed in annoyance and fell back onto her butt. The two were on Lucas’s bed, making use of a trip his parents had taken Erica on to finally test out the sex toy Max had spent her savings on.

Since Lucas had already thoroughly fucked all of Max’s holes a hundred times, Max thought it was time for her to fuck her boyfriend for a change. They had discussed it for a while, and Lucas had been surprisingly receptive to the idea, even a little eager to get fucked in the ass by his girlfriend. Unfortunately, the big black strap-on that was currently the only item of clothing the two had on between them was simply too thick and rigid to penetrate his virgin butthole.

“Are you absolutely sure you can’t handle it? Max asked with disappointment. “I can eat you out again to get you wetter.”

Lucas groaned. “It’s not the lube. We’ve already tried spit, cum , juices and even piss. The problem is it’s just too big.”

Max groaned as well. “There’s no way we can return this thing now, and I spent four months’ allowance on this dong!”

Lucas thought for a second. “Well it’s not necessarily entirely useless. If we could try something smaller first, maybe my ass could gradually get used to bigger stuff until it fits.”

Max shook her head. “We don’t exactly have the money to buy a smaller dildo.”

The two sighed again as they thought it over. Then an idea hit Max. “Unless…”

Lucas was confused. “Unless?”

Max got a mischievous grin. “What if we don’t need another sex toy? What if we use the real thing?”

Lucas was still confused. “Uh, sorry to burst your bubble, but you don’t exactly have a real dick, Max.” He stared at her exposed pussy beneath the strap-on in confusion.

Max groaned in disbelief at how dense her boyfriend could be. “I mean get another guy, stalker!”

Lucas’s eyes widened. “Holy shit, are you serious?! Who would we even ask?”

Max smirked again. “Well I know Billy’s always willing to fuck pretty much anything that moves.”

Lucas grimaced. “Uh, any other ideas before we resort to _him_?”

Max laughed. “Yeah, I didn’t think you’d go for that.” She thought for another moment. “Well, think any of the other nerds would be into it?”

Lucas blushed. “I mean, probably Dustin. Even if it’s just for science. Honestly Will too, he’s always staring at our asses when he thinks we’re not looking.”

Max grinned upon learning all of this. “Well that’s two dicks to try out. What about Mike?”

Lucas thought it over. “Honestly, even if he denies it, I bet he’d do anything to get laid. It’d probably make him whine less too.”

Both of them laughed, knowing how moody their party’s leader had been since he hit puberty. Once they had calmed down, Max reached for the radio.

Lucas’s eyes widened. “Wait, are you calling them right now?”

Max looked at him like he had two heads. “Of course I am. We have the house to ourselves for the whole day. I’m not wasting another minute that I could spend buried in that sexy chocolate ass of yours.” Lucas couldn’t help but shyly grin as she made the call.

An hour later, three blushing teens were standing in front of the naked couple, still sitting shamelessly on Lucas’s bed. All three were rock hard in their shorts.

“You want us to _fuck_ Lucas in the ass?!” Mike’s voice almost broke from how scandalous he made the idea sound.

Max grinned. “Just a few times, to loosen him up a little. But not too much. I still want to feel these ass cheeks squeezing my big plastic dick.” She playfully slapped her boyfriend’s ass as she gestured to the sex toy now resting on the bed.

Before Mike could protest again, Dustin spoke up with a smile on his face. “Hey, if he’s up for it I’m always glad to help a friend.” The others could tell by the tent in his shorts that he wasn’t just agreeing out of charity. By the time the others could speak, he was already stripping down to his socks.

Will stared at his curly-haired friend’s exposed body as he spoke next. “I-I mean… i-if you really want us to...”

Mike still wasn’t budging. “What do we even get out of this?”

The redhead glared at him. “Well besides just being good _friends_ …” She paused as she saw a bit of shame sink in for Mike at that comment. “...I’ll fuck all three of you once he’s properly stretched.”

Even though he tried to hide it, Mike’s mouth visibly uncurled upon hearing the reward, both that and the twitching bulge in his shorts giving away his interest. “F-fine… B-because we’re friends…”

Max clapped her hands together as she stood up, her C-cup breasts jiggling a little with each movement, which only increased all four of the boys’ erections. “Great, so if you could all strip, we can get started.”

Mike raised an eyebrow. “Wh-why all of us? Dustin already agreed. Why not just use him and get it over with?”

The redhead sighed. “Come on, you nerds are supposed to be smart. We have to do this scientifically. Start with the smallest and gradually work our way up so Lucas’s sexy behind her can get used to fat pulsating rods pounding his insides.”

Lucas had never blushed harder as he heard his girlfriend describe him this way to their friends. His cock was also leaking pre from excitement.

Max continued. “And looking at Dustin’s monster right here, I’d say there’s a good chance he’ll be going last.”

Dustin grinned with pride as his thick seven and a half incher pointed almost straight upwards, his own pre glistening on his exposed tip.

Mike blushed at the implication he was smaller. “Wh-what makes you think I’m not bigger?”

Max wasn’t gonna play along with his attempts to delay the inevitable. “Just get naked already and we can decide it once and for all.”

Having been shut up twice, Mike finally gave in and started stripping, with Will quickly following his lead. Within a couple of minutes, the only garments remaining on any of the teens’ bodies were three pairs of socks, and every cock was rock hard.

Just from looking at them, Max could already tell that Dustin was the thickest, though Mike certainly had him beat lengthwise. But she wanted to be absolutely sure before Lucas got his anal virginity taken.

“Get closer together. We want accurate results, right?”

The three boys blushed again, with Dustin still holding onto his big goofy grin while Will had a shyer smile. He had already guessed that he was probably the smallest of his friends, but at least his dick seemed to be thicker than Mike’s. The three awkwardly shuffled together, gasping as Max took hold of their cocks to closely compare them.

“Well, Lucas’s fat chocolate rod is around 8 inches long and 6 and a half inches thick.” She turned over her shoulder to admire it, prompting Lucas to grin and stroke it a few times for show. “Based on that, I’d say…” She took a few more looks back and forth as she thought over the numbers.

“Will, you’re probably around 7 inches long and 5 and a half thick. Dustin is really leading the pack with 7 and a half long and I think 7 thick too. I’ll have to try fitting this in my mouth later.” She winked at the curly haired boy she knew still had a massive crush on her.

Mike groaned, his arms crossed tightly as his cock throbbed anxiously. Max rolled her eyes. “I’m getting to you, Wheeler.” She grasped his long pale member and decided to tease him a bit, feeling it with both hands and turning it in every position she could think of, even caressing his balls. Soon he couldn’t help but let out a moan, satisfying her urge to get him to drop his “above-it-all” attitude for even a second. “Huh, you actually have Dustin beat in the length department at around 8 inches. Damn, you almost give Lucas a run for his money.” She smirked as she looked up at him again. “It’s too bad you’re really losing in the girth department. Only 5 thick.”

She gave a playful disapproving shake of the head as Mike stewed a bit. “Th-that’s average!” His friends couldn’t help but snicker. Lucas finally spoke up, having spent the past few minutes stroking himself to the sight of his friend’s impressive boners. “It’s nothing to be ashamed of, Mike. You just have to get used to the fact you have some above average friends.”

The four laughed harder as Mike glared at him. “Whatever, since I’m so fucking small I guess I should just get it over with and fuck him first, right?”

Max couldn’t help but recognize a bit of eagerness in his voice as she finally let go of his cock, it bouncing back to its usual position pointing straight forward as his pre dripped to the floor. “Not so fast. While it’s true preparing him for the strap-on is mostly about girth, his precious little butthole isn’t exactly ready for 8 inches impaling him lengthwise either. I figure we should average them out. Start with Will, then Mike and finally Dustin.”

“Whatever…” Mike grumbled to himself as he stepped back, trying to keep his hands off his cock even as he felt it throb. Dustin smirked as he put his hand on Mike’s shoulder. ‘I know it’s tough to wait for a chance at that chocolate ass, but I bet it’ll feel even better after Will gives it a good tenderizing.”

Still bright red with embarrassment, Will stepped forward, stroking his member a few times in preparation. Lucas grinned shyly as he realized this was real. He was seriously about to take his friends’ dicks up his ass. He got up on his knees and turned around, leaning on his elbows so his ass was up in the air. “Is this position good, Will?”

Will wasn’t expecting the question, and it took him a second to stop staring at the delicious brown ass-cheeks beckoning him forward to stutter out a “Y-yeah…” He slowly lifted his cock up and placed the tip against Lucas’s entrance, causing both to gasp from the contact on their sensitive body parts. The cleric slowly rubbed his member up and down the puckered hole, spreading his precum around in preparation.

Not able to see behind him, Lucas’s cock was throbbing in suspense for the moment Will popped his anal cherry, and was surprised when the movement suddenly stopped, only for the cock head to suddenly pull away.

“Will, what are you dooo-ooooooohhhhh!” Lucas’s question was interrupted by the sudden feeling of Will’s index finger entering his ass. The smallest party member had given himself a couple of strokes to spread his precum across his fingers before pushing one inside his friend’s butt. “S-sorry, I-I just wanted to make sure you were slick enough…”

Lucas grinned a bit as he recovered from the pleasurable surprise. “Damn man, you’re really prepared. Are you sure you’ve never fucked an ass before?” Will blushed. While he was 100% a virgin, the boy had spent a great deal of time imagining his friends fucking him from behind, and in doing so he’d also put a lot of thought into lubing up his own tight hole. “J-Just don’t want it to hurt…”

Max and Dustin both smirked at their shy friend as he generously lubricated Lucas’s hole, adding a second finger to further spread it before he felt it was sufficiently wet. Then it was finally his cock’s turn, and he returned his throbbing member to its original position between Lucas’s cheeks. “R-ready?”

Lucas grinned to himself. “Ready!” And then Will thrust his hips forward. Lucas gripped the bedsheets tightly as he winced in a mixture of pain and pleasure. His knees shook as his ass instinctively thrust backwards, meeting Will’s groin as he thrust all 7 inches of hot throbbing Will the Wise wang into his backside. Will gasped in surprise as he looked down, shocked to see Lucas’s cheeks pressed directly against his trimmed pubic hair and balls. The cleric had intended to go slowly, but the intense feeling of losing his virginity and Lucas’s tight hole milking his rod had caused him to thrust all the way in immediately.

Lucas was still groaning as he got used to the feeling, his whole body quivering as he processed the sensation of his friend’s fat shaft filling his stomach. Slowly though, the pain was fading, and it was certainly a lot easier to take in than the rigid plastic sex toy had been.

“L-Lucas, a-are you okay?” Will’s voice quivered as he worried he had hurt his friend. But Lucas finally spoke up. “Y-yeah, j-just takes a little getting used to…” The bowlcut-headed boy sighed in relief, glad he could just focus on the pleasure of fucking someone for the first time.

He started to move, slowly at first, pumping his hips back and forth. He let just about half of his cock, now completely slick with his own pre, slip out of Lucas’s tight hole. Even this was almost as difficult as putting it in, as Sinclair’s ass felt like it was fighting to hold onto its hot throbbing plug. Then Will thrust it back in, enjoying the satisfying slap of his tight sack against the bottom of his friend’s sweaty ass cheeks.

It didn’t take long before the two worked up a rhythm, with Will slamming his hips forward as Lucas thrust his ass backward to meet him, both gasping in pleasure as they enjoyed their respective first times with anyone/another guy. Just as Will was starting to get used to the sensations making him moan, he let out an even more intense utterance as he was surprised by a feeling against his own butt.

He turned over his shoulder to see that Max had gotten on her knees behind him, her warm hands spreading his own pale cheeks apart to get a good look at his virgin asshole. “Don’t mind me, I’m just giving you a little incentive to fuck my stalker a little harder.”

Will turned back to the task at hand, bracing himself for the feeling of the redhead’s fingers in his hole. But the cleric almost leapt into the air, lifting himself up onto his toes and moaning like a girl as his butthole was instead invaded by Max’s tongue.

Dustin and Mike stared in awe as they watched Lucas’s girlfriend bury her face in Will’s ass, each hand getting a good hold on a cheek while her nose and mouth took in the scent and taste of his insides. Fingering himself in bed was nothing compared to this new sensation, and Will continued to stand on his toes, thrusting even deeper into Lucas as he himself got tonguefucked from behind.

Unable to stand not touching himself, Dustin finally took hold of his own cock and started to masturbate to the insanely hot sight of the ass-themed threesome in front of him. “Fuuuuuck, Will! Finish Lucas off already! I need a turn before I blow just from watching!”

Mike was still trying to appear disinterested, keeping his arms folded even as his dick twitched with impatience, drops of pre staining the bedroom floor below. “H-how does it feel, Will?”

Will could barely form words at this point, but he managed to sneak a “S-soooo g-goooood!” in between his moans as Max hungrily stirred her tongue around his insides. Mike blushed harder as he couldn’t help but imagine getting his own ass eaten out, and his butthole twitched at the thought.

By now, both Will and Lucas were on the edge. “I-I’m g-getting close, Lucas!”

Lucas grinned as he turned his head a bit to look Will in the eye, still gripping the sheets for support as Will rode him. “Do it, man! Pump me full of your hot cum!”

Just as those intensely sexy words hit Will’s ears, Max expertly pressed her tongue as deep as possible, stimulating him more than he could ever imagine. The smallest member of the party let out a long gasping moan as he bucked into the tight chocolate ass one last time and then erupted his hot cream deep inside the waiting hole.

Lucas let out one last “Fuuuuuck yeah!” as the first of his three friends bred his butthole, and the feeling of the hot liquid deep inside him made him climax as well, bucking his own hips as his thick cock pumped a creamy load into his bedsheets hands-free.

Max withdrew her tongue as she leaned back to enjoy her handiwork, absentmindedly playing with her soaking wet pussy as she watched Will’s soles drop back the floor. The smaller boy’s legs wobbled as he held onto his friend’s ass for support for a good couple of minutes, and then finally pulled out as he regained his strength.

Will’s cock had softened completely, the intense orgasm having drained him completely for the moment, and he almost stumbled backward as he watched the intensely sexy sight of his hot cum leak out of Lucas’s butt.

Both boys were surprised as Max started to clap. “Great show, Will! You really taught stalker over there’s asshole a lesson.” Will blushed as he returned to stand with his other friends. Max looked over her shoulder. “Mike, I believe it’s your turn.”

Mike continued to try and look aloof, rolling his eyes as he stepped forward. “Let’s get this over with…” But he barely moved before he was surprised by a slap on the ass, making him gasp as he stumbled forward, almost falling on top of Lucas. He turned back to see a giggling Dustin still stroking himself. “What? I just wanted to keep this moving. Lucas wouldn’t like it if I wasted my load all over his floor, right?”

Lucas laughed as well, having gleaned what happened from the sound effects. “Damn Mike, you’re so eager to fuck me you missed my hole completely!” Mike glared at him as he lifted himself back up to his feet, his cock having rubbed against Lucas’s lower back as a result of his stumble.

“You’re not gonna be laughing once I fuck you speechless.” Mike’s usually whiny tone had a hint of dominance in it as he took in the view of Lucas’s ass, finally taking hold of his cock with one hand to be sure he was fully hard, though he had in fact been fully erect from the moment he stripped.

Lucas turned back and grinned. “Why? You gonna fuck me silly with that skinny thing?”

The sound of another slap filled the room as Mike suddenly spanked one of Lucas’s ass cheeks, causing Lucas to moan in both pain and arousal as his cock stiffened again.

“Fuck yeah, I am!”

Lucas’s eyes widened as he realized Mike was seriously getting into this, and he spotted a grin forming on the dark-haired boy’s freckled face before his thumbs stretched the chocolate asshole wide. Using Will’s leaking cum as lube, Mike didn’t even bother wasting a second preparing Lucas’s hole, and the bottom boy gasped as the paladin’s cock quickly invaded his sensitive hole.

Both boys let out long groans of pleasure as Mike instantly stuffed all 8 inches of his meat into his oldest friend’s tight butthole. “You like that, Sinclair?”

Lucas knew Mike could be demanding, but he never expected him to be this sexually dominating. He could almost rival Max on one of their kinkier date nights. “I-is that the best you can do, Wheeler?” Though Mike wasn’t as thick as Will, the extra half an inch buried deeper in his asshole was making this session just as surprising as the first. Lucas wasn’t going to give his friend the satisfaction he was looking for without a little more effort though.

“I-I’m just getting started!” Mike quickly got to work, adapting to the feeling of his friend’s tight walls squeezing his dick more quickly than Will had. While Mike was just as new to anal as his smaller friend, he at least had the experience of fucking El’s pussy to prepare him. It wasn’t long before Mike was slamming into Lucas at full speed, the two continuing to trade insults between moans.

“Y-you call this tight? I bet you could fit two of those dildos in here!”

“D-don’t worry, there’d still be some extra room for that limp noodle of yours to sneak in too!”

Max rolled her eyes as she listened to the two. “Boys are such losers…”

Meanwhile, both Dustin and Will had resumed stroking themselves to the show. The sight of Mike’s pale ass bouncing with each movement had quickly returned Will to full length, and his eyes were glued to his dark-haired friend’s cheeks as he stroked himself in time with their vigorous thrusts.

The view didn’t last long however, as Max quickly took the same position she had with Will, spreading Wheeler’s freckled ass cheeks and getting her third taste of ass that afternoon.

Mike let out a long high-pitched moan from the sensation, so lost in hatefucking his friend to notice the redhead sneak up on him. Lucas snickered between moans. “Damn dude, are you really a girl? This would be a lot more impressive if that’s your clit you’re fucking me with…”

Mike blushed harder, realizing how embarrassing his still pubescent voice could be at times, but there was no way he was going to let his friend emasculate him while his cock was deep in his ass. Soon even Max was having trouble tonguing his hole as Wheeler’s hips seemingly doubled in speed and intensity, slamming his long throbbing member deeper and deeper into Lucas, his balls slapping against his friend’s sack and his tip teasing the dark-skinned boy’s prostate with each motion.

Soon their voices were completely devoted to moaning as they fucked insatiably, with Mike even lifting one leg onto the bed to fuck his friend deeper, one hand grasping the sheets for balance as his own sweaty chest pressed against Lucas’s back.

With his legs spread wider though, Max found it easier to explore his virgin asshole, and the sensation of her tongue on his prostate was quickly becoming too much to endure. Just a little over a minute after changing positions, Mike let out a low growl resembling the words “T-take it!” as he finally let loose, pumping burst after burst of thick jizz deep into his friend’s cock-hungry ass.

Lucas himself finally collapsed his face and chest against the bed, letting the warm sensation of Mike’s body against his wash over him as he once again creamed his own bedsheets. His second load was even larger than the first, as Mike’s passionate lovemaking had driven his prostate wild.

The two laid still for a minute, catching their breath, before they were finally roused by Max’s voice. “Are you two lovers gonna cuddle like that forever, or is Dustin gonna get his turn?”

Mike turned red again as he leapt to his feet, letting another load of cum leak from Lucas’s ass as he sheepishly returned to his other friends, avoiding eye contact as he was suddenly reminded that they had watched his entire display.

He shyly placed a hand over his softening cock, as if the other four hadn’t already gotten a good long look at it. Dustin continued to grin and slapped him on the back. “That was fucking awesome! You’ve gotta fuck me like that sometime!” Mike only gave him a silent glare, though the thought honestly did interest him a little. He’d have to think it over.

Max looked at Dustin. “And now for the grand finale.” She motioned towards Lucas’s still recovering body. “Your throne awaits, oh girthiest of the nerds.”

Dustin’s smile only widened as he approached his twice-fucked friend, continuing to stroke himself slowly, having been edging himself ever since he stripped. To the surprise of the others, Dustin started by grabbing hold of Lucas and turning him over. The dark-skinned boy was confused, but too tired to resist, and rolled over to expose his front. His sexy toned chocolate chest was soaked in sweat with streaks of the cum he had erupted. He grinned at Dustin as he spread his legs wide.

“What? Need to see my pretty face to get it up?”

Dustin continued to grin. “I want to see the faces you make when you get the best ass-fucking of your life.”

All four of Dustin’s friends were surprised when the curly-haired boy proceeded to drop to his knees, grasping Sinclair’s thighs as he buried his face in the boy’s ass. Max’s jaw dropped as Henderson got to work eating Lucas’s ass, slurping up the excess cum of both Will and Mike and thoroughly lubricating Lucas’s intensely sensitive hole with his saliva.

“H-holy fuck man, that feels amazing!”

Dustin paused to smirk at him. “I’m a professional. I want you begging for me to make you explode even before you feel my dick.” He got back to work, burying his tongue deeper than even Max had ever managed. Dustin had never told his friends about most of the activities he had taken part in at Camp Know Where, but needless to say, they had taught him countless ways to pleasure teens, regardless of gender.

Within seconds, Lucas’s cock was back at full attention, dripping precum all over his sweaty chest as it twitched obscenely. Just as Dustin had promised, he was aching to be fucked again. Even after two hands-free orgasms he was starved for a third.

Slowly, Dustin stood back up and admired his handiwork. He had never seen Lucas so vulnerable and horny. He looked like an animal in heat. “You want this?” He grasped his fat cock and wiggled it around.

“Fuck yeah, Dustin! Fucking breed me!”

Those were exactly the words the curly-haired boy was waiting to hear. Unlike his friends, Dustin got to work slowly. His cock slid into Lucas’s still intensely tight butthole inch-by-inch. The wait was agonizing for the bottom, who bucked his ass toward his friend in a fruitless attempt to get it all inside him faster. But the wait was absolutely worth it, as the sensation of 7 and half inches of throbbing meat stretched Lucas’ hole the widest it had ever been.

Then Dustin really got to work. His first thrusts were just as slow and methodical as his entry, bucking into Lucas like a gentle wave on the beach. Behind him, Max took up her position for the third time, eager to please Dustin’s ass just as he was currently pleasuring her boyfriend.

Henderson had already experienced the joy of a tongue buried in his thick bubble butt – among other larger appendages – but he was enjoying the sensation nonetheless, especially as the first rimjob from his first crush. He would have to compare Suzie’s technique sometime in the future. Dustin began to let out long slow moans to join the more intense ones escaping Lucas’s lips as he sped up his thrusts, gradually increasing to the speed with which Will had fucked the same hole earlier.

The show was intensely erotic for the entire party, as Will continued to stroke his already cum-soaked cock and Mike quickly gave in to the temptation to jerk off his as well, having returned to full length during Dustin’s foreplay. The sensual way Dustin’s hips bucked against Lucas’s was filling the freckled boy’s head with ideas he never thought he’d consider before. He reached up to fondle one of his nipples and bucked his hips against his hand, fucking his fist as he imagined Dustin pounding his ass in the same way.

Meanwhile, Lucas was practically drooling from the most intense pleasure he had ever felt. He had been prepared for taking Max’s strap-on as a fun little experiment, but he had never expected being fucked in the ass could be so amazing. His cock was throbbing more than it ever had in the past, precum continually oozing from the tip and dripping onto his abs as he struggled to hold in his own climax. Dustin was still increasing speed, approaching that of Mike’s earlier wild fucking with the added bonus of his fat cock more consistently hitting his prostate.

Pretty soon, Lucas couldn’t take it anymore, and Dustin could tell. The dark-skinned boy bit his lip, bucking his ass desperately against the bard’s shaft, aching to explode. Dustin grinned. “Ready to cum?”

Lucas nodded furiously, his eyes alone communicating how badly he needed to finish. “F-fill me up, Dustin…”

Dustin quickly obliged, pulling out and slamming all the way in one last time. The sensation of his fat cock against Lucas’s prostate finally made the ranger lose all control, and his cock twitched violently as he erupted burst after burst of hot thick seed all over his own stomach, chest and even face. If his friends hadn’t known better, they’d think he’d been holding this load in since he first hit puberty.

Satisfied with his results, Dustin finally let loose as well, continuing to buck his hips and extend Lucas’s explosive climax while releasing his own hot load deep into his ass. Max’s tongue in his ass only increased the pleasure as he pulled out, letting the excess cream spill out of Lucas’s thoroughly stretched asshole as he milked the last few drops out with his hand, letting it coat Lucas’s tight chocolate balls and cock.

Still semi hard, Dustin returned to the lineup, grinning ear to ear as he saw the looks of awe on Will and Mike’s faces. Even Max was wide-eyed at how thoroughly spent her boyfriend looked, soaked in two loads of cum with the remains of another three leaking out of his ass.

“W-wow, I, uh, I honestly didn’t think that would be so fucking hot!” Max slowly stood up, her legs weak from edging herself since she first unpackaged the strap-on that morning. The boys all stood in awe as she continued to rub her pussy, her juices having formed glistening streaks all the way down her thighs and her clit clearly engorged.

“I’m not even sure if he’d be up to trying out the strap-on at this point…”

Lucas finally spoke up. “N-no way. I didn’t go through all that just to leave you unsatisfied, babe.”

All four of Lucas’s friends turned to look at him in surprise. He was still trying to give off an air of strength and suavity for his girlfriend, even as his body gave off the air of a freshly-fucked slut.

“Are you sure about that, stalker?”

Lucas slowly lifted himself to his feet and began to stretch, not ready to give up yet. “Put it on, Max. My ass is all yours.”

As the redhead grabbed the toy and affixed it around her waist, Mike suddenly remembered the terms of their agreement. “Wait, isn’t it _our_ turn to fuck _you_ now?”

Max smirked as she turned back around, and reached down to spread her pussy lips, still exposed beneath the device. “Who said I can’t do both at the same time?”

Within a minute, the party of five horny teens had worked out their positions. Mike lied down on the floor, face-up, as Max prepared to lower herself onto his swollen 8-inch cock. Both let out a long slow moan as the redhead’s soaked cunt slid down onto his already cum-covered rod, the excess lubrication letting her take the whole length in immediately. Max turned to look over her shoulder and beckoned Dustin to take his position.

The curly-haired boy dropped to his knees and grinded the fat bell end of his cock against her tight little asshole. Normally, he’d give Max the full rim job experience before sliding his thick rod into her butt, but he had already used up quite a bit of energy on her boyfriend. For now, he lubed up her back entrance with the mixture of the boys’ cums on his shaft before thrusting inside, barely able to fit all 7 and a half girthy inches as he felt Mike’s rod almost rubbing up against his through the barrier inside her.

Will stood back, knowing he wouldn’t be able to access his hole of choice until Lucas took his position. Max stroked the thick plastic rod between her legs, spreading around the thick coat of lube in preparation to impale her boyfriend. The dark-skinned boy dropped to his knees, gasping at the feeling of the cold plastic against his backside, before looking down to see Mike’s pale naked body just below him. The tip of his chocolate cock rubbed against the paladin’s stomach, smearing excess pre around his already creamy white skin.

“Are you sure you’re ready?” Max checked one final time as brushed the sex toy up and down her boyfriend’s delicious-looking ass.

“As ready as I’ll ever be!”

Mike could tell Lucas was still a little nervous, but after taking three real cocks of varying size, Lucas knew it was time to take the monster strapped to Max’s groin. The ranger closed his eyes tight and braced himself. Finally, the zoomer spread his back entrance open and thrust her hips in. Going for more of a Will approach than Dustin’s, Max quickly pushed all seven inches of the fat synthetic cock into her boyfriend’s hole, eliciting a long deep moan from his other end. It hurt at first, but nowhere near as much during their first attempts. Soon his ass relaxed around the lubricated phallus and he knew that the practice each of his friends had given him had done its job.

Slowly, the three boys and one girl began to move. Mike’s ass bucked off the floor as his cock slammed into Max’s pussy while Dustin ground his own hips against Max’s behind, making her shake in pleasure as she was double-stuffed for the first time. The pressure from Dustin also pushed her forward, hitting Lucas’s deepest points as he bucked his cum-soaked ass cheeks against her hips in response. Though disjointed at first, the four quickly found a rhythm, pumping in and out of each other’s tight aching holes perfectly in sync

Among the cascade of moans, Max turned to beckon Will over, the smallest boy having been stroking his cock in anticipation as he watched his friends accustom themselves to each other’s bodies. The redhead opened her mouth wide, expecting the cleric to slide his throbbing member down her throat, but she was surprised when he instead approached Lucas.

“W-would you mind blowing me, Lucas?”

Lucas was stunned for a second. Before today, he would never have imagined the meek little Will Byers requesting a blowjob from him. Of course, he also never would have expected to be fucked by his girlfriend while she was DPed by Mike and Dustin shortly after he had taken all three of his friends’ cocks.

The dark-skinned boy grinned. “Of course.” Then he opened wide. As impatient as ever, Will quickly grabbed hold of his friend’s head and stuffed his swollen member in his mouth. It took a second for Lucas to adjust to the feeling of a cock down his throat, but he quickly got to work sucking on it, surprised by how much he enjoyed the sticky pre-and-cum-soaked member fucking his mouth.

Already lost in the pleasure of the ongoing fivesome, Mike looked up at Will’s smooth ass hovering above and thought to himself “Fuck it.” He reached up and pulled the smallest boy downward, Will immediately taking the hint and sitting on Mike’s face. Spreading the soft pale cheeks, Mike got to work tonguing his friend’s virgin hole, just as Lucas’s tongue was exploring every inch of Will’s cock on the other end.

When Will later described the fivesome to Jonathan that night, his older brother cursed the fact he wasn’t there with his camera. The sight of these five horny 14-year-olds would surely have been a best-selling porno. Max bounced on both Mike’s and Dustin’s cocks, feeling them almost grind against each other inside her tight aching holes. Lucas slammed his ass against Max’s strap-on, moaning against Will’s cock in his throat every time the plastic rubbed his prostate. Mike explored every inch of Will’s delicious asshole as he bucked his hips into Max’s soaked pussy. Dustin fucked Max’s tight asshole slow and sensually as he groped her soft tits from behind. And Will furiously fucked Lucas’s throat as he rode Mike’s face. All five teens were lost in pleasure, sucking and fucking and licking and fondling and moaning for what felt like an eternity.

As expected of five relatively inexperienced teens though, the party couldn’t hold in their climaxes forever. Mike’s tongue finally proved too much for Will to handle, causing the cleric to erupt into Lucas’s mouth. The ranger hungrily swallowed every drop of the thick cream, sucking any extra drops off his softening shaft as he felt his own orgasm wash over him. The thick dildo in his ass pushed him over the edge, making him erupt hands-free for the fourth time that day as he shot another thick geyser of spunk all over Mike’s pale chest. Lucas instinctively thrust his ass backwards as he came, causing him to push Max backwards as well. The zoomer felt herself impaled even deeper by the paladin’s and bard’s cocks and she couldn’t hold on any longer. Her pussy and asshole both tightened around the fat shafts inside her as her juices gushed out, squirting intensely all over her boyfriend’s ass and leaking down onto Mike’s shaft and pubes. Finally, Mike and Dustin felt Max’s tightened holes start to milk them dry and they exploded simultaneously inside her cunt and asshole, pumping both ends full of their thick and creamy cum as they instinctively bucked into her one last time.

The fivesome quickly became a heap of sweaty cum-soaked teens as they recovered from their intense orgasms, cocks softening as the last of their loads dripped out and asses recovering from being pounded. Their bodies thoroughly exhausted by the day’s events, the teens all felt like they could lie like this forever.

Then Erica’s voice echoed across the house. “Hey nerd, we’re home!”

**Author's Note:**

> I originally intended this to be the next chapter of Stranger Things Smutty One-Shots, but it ended up becoming way longer so I made it its own thing. I still plan on using some of the ideas people have commented though, so don't worry!


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